271 total properties
Did you mean the neighborhood Winchester?
View 250 Duclair Drive Winchester, KY MLS# 22024097
$110,000
Studio

Beds

0.0

Baths

250 Duclair Drive

Winchester, KY

Bluegrass
View 260 Duclair Drive Winchester, KY MLS# 22024098
$110,000
Studio

Beds

0.0

Baths

260 Duclair Drive

Winchester, KY

Bluegrass
View 255 Duclair Drive Winchester, KY MLS# 22024102
$110,000
Studio

Beds

0.0

Baths

255 Duclair Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 139 Jacob Court Winchester, KY MLS# 22024111
$110,000
Studio

Beds

0.0

Baths

139 Jacob Court

Winchester, KY

Bluegrass
View 135 Jacob Court Winchester, KY MLS# 22024112
$110,000
Studio

Beds

0.0

Baths

135 Jacob Court

Winchester, KY

Bluegrass
View 125 Jacob Court Winchester, KY MLS# 22024114
$110,000
Studio

Beds

0.0

Baths

125 Jacob Court

Winchester, KY

Bluegrass
View 115 Jacob Court Winchester, KY MLS# 22024116
$110,000
Studio

Beds

0.0

Baths

115 Jacob Court

Winchester, KY

Bluegrass
View 400 Wexford Drive Winchester, KY MLS# 26000557
$110,000
3

Beds

1.1

Baths

1,260

Sq.Ft.

400 Wexford Drive

Winchester, KY

Bluegrass
View 7950 Four Mile Road Winchester, KY MLS# 25503896
$123,000
Studio

Beds

0.0

Baths

7950 Four Mile Road

Winchester, KY

Bluegrass
View 1940 Athens Boonesboro Road Winchester, KY MLS# 25012636
$125,000
Studio

Beds

0.0

Baths

1940 Athens Boonesboro Road

Winchester, KY

Bluegrass
View 110 Knox Court Winchester, KY MLS# 25503832
$129,300
Studio

Beds

0.0

Baths

110 Knox Court

Winchester, KY

Bluegrass
View 122 Callaway Street SE Callaway Street Winchester, KY MLS# 26000228
$129,900
2

Beds

1.0

Baths

876

Sq.Ft.

122 Callaway Street SE Callaway Street

Winchester, KY

Bluegrass
View 103 Yorktowne Court Winchester, KY MLS# 25500573
$130,000
3

Beds

1.0

Baths

1,150

Sq.Ft.

103 Yorktowne Court

Winchester, KY

Bluegrass
View 19 Hughes Avenue Winchester, KY MLS# 26004216
$130,000
3

Beds

2.0

Baths

1,232

Sq.Ft.

19 Hughes Avenue

Winchester, KY

Bluegrass
View 12569 Ironworks Road Road Winchester, KY MLS# 25002394
$137,500
Studio

Beds

0.0

Baths

12569 Ironworks Road Road

Winchester, KY

Bluegrass
View 9 Linden Avenue Winchester, KY MLS# 25007762
$139,000
2

Beds

1.0

Baths

886

Sq.Ft.

9 Linden Avenue

Winchester, KY

Bluegrass
View 3208 Ford Hampton Road Winchester, KY MLS# 25506476
$139,000
2

Beds

1.0

Baths

807

Sq.Ft.

3208 Ford Hampton Road

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 150 Cook Avenue Winchester, KY MLS# 25015192
$144,000
3

Beds

1.0

Baths

805

Sq.Ft.

150 Cook Avenue

Winchester, KY

Bluegrass
View 228 Jackson Street Winchester, KY MLS# 25015194
$146,000
3

Beds

1.0

Baths

1,020

Sq.Ft.

228 Jackson Street

Winchester, KY

Bluegrass
View 1030 Craig Crossing Road Winchester, KY MLS# 22004993
$150,000
Studio

Beds

0.0

Baths

1030 Craig Crossing Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

266

Estimated median home price

$285,000
Winchester KY Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winchester, Kentucky real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winchester, KY.

Homes for Sale by Price in Winchester, KY

PriceCount
$0 - 100K30
$100K - 200K54
$200K - 300K61
$300K - 400K37
$400K - 500K18
$500K - 600K13
$600K - 700K11
$700K - 800K11
$800K - 900K7
$900K - 1M4
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family145
Townhouse5
Condo0
Commercial13
Rental15
Lots and Land78
Condo/Town/CoOp0
CoOp0
Multi Family13
Mobile Home0
Farms12

(Data as of 3/18/2026)

Information deemed reliable but not guaranteed.

Listing data provided courtesy of the Internet Data Exchange Program of Bluegrass REALTORS.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Bluegrass REALTORS. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 3/20/2026.